Is it causing prices to go up like foreign investments are running up the values in Chicago?

Cause Charles is right, it's not easy to find a deal there.

This is the area you are investing in and these little things work for me and I have the best tenants cause I try to be the best landlord. 

The effects of reckless lending then caused a leveling followed by crash. 

That makes me work hard to get good tenants on the front end and then rewards me the few times that a good tenant is late and it throws off my processes and causes me lots of extra work.

When you offer 12 month or less leases you can get rid of people who don't fit well or who cause "trouble" more readily.

I am working hard to grow my investing business but due to still having my 9 to 5 I am not able to put in the necessary time to manage my projects and subs as I should and This is causing my profits to go down and the time to complete the project to go up.

I am concerned that scaling to this level will cause the system to break.  

The story is pretty typical: inherited tenant did not report leaking bathtub faucet, it caused water damage downstairs and was reported by the tenant from below.

You can stay on top-of-mind for when they are ready to list, and also not give them too much info that they'll have no reason to contact you (like Market Snapshot can cause).